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21 Questions to Ask Your Girlfriend

Questions to ask your girlfriend and grow closer

The questions that land best with a girlfriend are specific and a little brave: not "how was your day" but "what is one thing you are glad you did not post online." This set is built to start those conversations.

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21 Questions
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Question #1

What is one memory of us you go back to when you need a smile?

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105 questions
#1
easy

What is one memory of us you go back to when you need a smile?

Follow-ups: Why that one? • When do you need it most?
#2
easy

What was your honest first impression of me?

Follow-ups: How wrong were you? • What took the longest to figure out?
#3
medium

What is something I do that makes you feel safest?

Follow-ups: When did you notice? • Do I do it on purpose?
#4
medium

When did you first realize I was more than a friend?

Follow-ups: Was it a moment or a feeling? • Did your friends know first?
#5
medium

What is your favorite thing about the way we talk things out?

Follow-ups: What do we do right? • What could be better?
#6
easy

What is one thing you want to do together every single month?

Follow-ups: Why monthly? • Which month starts it?
#7
easy

If our story was a movie, what scene would open it?

Follow-ups: What genre is it? • Who plays us?
#8
medium

How have you grown since we started dating?

Follow-ups: What sparked it? • Do you like who you are becoming?
#9
easy

What is your favorite nickname for me, and why?

Follow-ups: Where did it come from? • Which one do I hate?
#10
easy

What is one thing you tell your friends about me that makes them roll their eyes?

Follow-ups: Why do they roll their eyes? • What else is on the list?
#11
medium

What is the most yourself you have ever felt with me?

Follow-ups: What was happening? • How can we get there more?
#12
medium

What is something you want me to never forget about you?

Follow-ups: Why is it important? • Do I know it yet?
#13
easy

What is one thing of mine you love wearing or borrowing?

Follow-ups: Why that one? • Will you ever return it?
#14
easy

What holiday do you want us to make unreasonably magical together?

Follow-ups: What would we do? • How far in advance do we start?
#15
easy

What is the most fun we have ever had on a date?

Follow-ups: What made it work? • Can we recreate it?
#16
easy

What is a tiny thing I do that you pretend to be annoyed by but secretly love?

Follow-ups: When did you start faking it? • Should I do it more?
#17
easy

What is one thing you wish I would say to you more often?

Follow-ups: Why that? • What stops me?
#18
easy

What is your favorite picture of yourself that I took?

Follow-ups: Why that one? • When do I take my best shots?
#19
medium

What is something you hesitated to share with me at first?

Follow-ups: What made you share it? • What else feels hard?
#20
medium

What do you think keeps us strong when things get busy?

Follow-ups: What do we do well? • What should we protect?
#21
medium

What is something you are proud of that you downplay?

Follow-ups: Why hide it? • Can I brag about you instead?
#22
medium

What is a worry I could help you carry right now?

Follow-ups: How can I help? • Why have you kept it to yourself?
#23
easy

What is the best choice you made for yourself this year?

Follow-ups: What made it hard? • What changed after?
#24
easy

What is something you loved as a kid that you still love?

Follow-ups: Why did it stick? • Do we do it together?
#25
medium

What is a compliment that stuck with you for years?

Follow-ups: Who gave it? • Do you believe it now?
#26
easy

What is something you are better at than you admit?

Follow-ups: Why do you hide it? • Who sees it in you?
#27
easy

What is one thing that instantly brightens a bad day?

Follow-ups: When did you last need it? • Can I do it right now?
#28
easy

What is one thing that drains you the fastest?

Follow-ups: How do you recover? • How can I protect you from it?
#29
medium

What is a fear you would love to leave behind this year?

Follow-ups: Where did it come from? • What is step one?
#30
medium

What is something you believe in that took courage to believe?

Follow-ups: What did it cost? • Who stood with you?
#31
medium

What is the hardest season you have ever pushed through?

Follow-ups: How did you get through it? • What did it leave you with?
#32
medium

What is one thing you wish you had known at eighteen?

Follow-ups: Why that? • Who should hear it now?
#33
medium

What is a moment that quietly changed your life?

Follow-ups: What happened? • Did anyone notice?
#34
easy

What is something you are becoming more confident about?

Follow-ups: What changed? • How can I cheer you on?
#35
medium

What is the most misread thing about you?

Follow-ups: Why do people get it wrong? • Do I read you right?
#36
medium

What is something you need more of from me?

Follow-ups: Why now? • What would it look like?
#37
medium

What is something you need less of from me?

Follow-ups: Why is it hard to say? • What replaces it?
#38
easy

What is a small gesture that always makes you feel seen?

Follow-ups: Who taught you that? • Do I do it?
#39
easy

What is the best advice you have ever taken?

Follow-ups: Who gave it? • What changed after?
#40
medium

What is one thing you want people to remember about you?

Follow-ups: Are you on track? • Does it matter who remembers?
#41
easy

What is one destination you have mentally already packed for?

Follow-ups: What is in the bag? • When are we going?
#42
easy

What would our dream home have that no other home has?

Follow-ups: Why that feature? • Where is it located?
#43
easy

What is one goal you want us to hit together this year?

Follow-ups: What is step one? • How do we celebrate?
#44
easy

What does a perfect slow morning with me look like to you?

Follow-ups: What is on the table? • What time do we wake up?
#45
medium

What is one thing you want to create with me someday?

Follow-ups: Why that? • What is the first step?
#46
easy

What milestone are you most excited for us to celebrate next?

Follow-ups: Why does it matter? • How will we mark it?
#47
medium

How do you imagine a random Wednesday with me in ten years?

Follow-ups: What stays the same? • What surprised you about your answer?
#48
easy

What is one hobby you want us to share?

Follow-ups: Why that one? • Who will be better at it?
#49
easy

What is something you cannot wait to show me how to do?

Follow-ups: Why that skill? • How patient will you be?
#50
easy

What is something you want me to help you learn?

Follow-ups: Why me? • When is lesson one?
#51
easy

What is one couple tradition you are jealous of and want for us?

Follow-ups: Whose is it? • How do we make it ours?
#52
medium

What is one rule you think keeps couples close?

Follow-ups: Why that rule? • Do we follow it?
#53
medium

What is something you want us to do less of?

Follow-ups: Why now? • What replaces it?
#54
easy

What is something you want us to do more of?

Follow-ups: Why that? • When do we start?
#55
medium

What is one thing about us you would never trade?

Follow-ups: Why is it sacred? • When did you realize it?
#56
easy

What is the most romantic thing you daydream about me doing?

Follow-ups: What is the plan? • Is it a secret?
#57
medium

What is one thing you wish you had said sooner in our relationship?

Follow-ups: Why did you wait? • Does it still matter?
#58
medium

What is one thing you wish I had said sooner?

Follow-ups: Why did I not? • What would have changed?
#59
medium

What is a promise you hope we always keep?

Follow-ups: Why is it sacred? • Have we made it out loud?
#60
easy

What is one thing you hope we never outgrow?

Follow-ups: Why does it matter? • When did it start?
#61
easy

If we had a walk-in song as a couple, what would it be?

Follow-ups: Who picks the tempo? • Where is the entrance?
#62
easy

If we pulled off a heist together, what would your role be?

Follow-ups: Who cracks under pressure? • Do we get away?
#63
easy

If we were snowed in for three days, what would we do first?

Follow-ups: Who makes the hot chocolate? • What is day three like?
#64
easy

If we auditioned for a dance competition, what song would we pick?

Follow-ups: Do we win? • Who leads?
#65
easy

If we could only share one dessert forever, what would it be?

Follow-ups: Who gets the bigger half? • What breaks first?
#66
easy

If we opened a shop together, what would we sell?

Follow-ups: Who runs the register? • What is the name?
#67
easy

If someone made a documentary about us, what would the title be?

Follow-ups: Who is interviewed? • What is the twist?
#68
easy

If you could relive one of our days, which one would you pick?

Follow-ups: Why that day? • What would you do differently?
#69
easy

If we learned one new language together, which would it be?

Follow-ups: Why that one? • Where do we use it first?
#70
easy

If I gave you one free pass to plan anything for us, what would it be?

Follow-ups: Why that? • When do we cash it in?
#71
easy

What is the silliest thing you have done to get my attention?

Follow-ups: Did it work? • Would you do it again?
#72
easy

What is one quirk of mine you find unreasonably attractive?

Follow-ups: When did you notice? • Do I know I do it?
#73
easy

What is one guilty pleasure you finally admit to me right now?

Follow-ups: How long have you hidden it? • Can we share it?
#74
easy

What is the most embarrassing story your best friend could tell about you?

Follow-ups: Is it true? • Can I hear it from them?
#75
easy

What is a trend you secretly wish would come back?

Follow-ups: Why did it die? • Would you wear it first?
#76
medium

What is one value you refuse to give up on?

Follow-ups: Where did it come from? • Has it been tested?
#77
medium

What is something you feel called to do with your life?

Follow-ups: What is stopping you? • How can I help?
#78
medium

What is one thing a past heartbreak taught you?

Follow-ups: How did it change you? • Are you grateful for it?
#79
medium

What is one thing you want your future family to feel like?

Follow-ups: What traditions matter? • What do I fit into?
#80
medium

What is something you think makes someone a truly good partner?

Follow-ups: Who showed you that? • Do you see it in us?
#81
medium

What is one thing from your childhood you want to carry forward?

Follow-ups: Why that thing? • What do you leave behind?
#82
easy

What is something we handle better than you expected?

Follow-ups: What is our secret? • Who taught us?
#83
medium

What is one question you wish I asked you more often?

Follow-ups: Why that question? • Ask me now?
#84
medium

What is a boundary you are thankful we respect?

Follow-ups: Why was it hard to set? • How did I respond?
#85
medium

What is something you forgave me for that I never noticed?

Follow-ups: Why keep it quiet? • Should I have known?
#86
medium

What is something you are learning to forgive yourself for?

Follow-ups: What would help? • Can I help carry it?
#87
medium

What is one thing we have that no amount of money could buy?

Follow-ups: When did you realize it? • How do we protect it?
#88
easy

What is the kindest thing you have ever done for someone?

Follow-ups: Why did you do it? • Did they ever find out?
#89
medium

What is something you will always defend?

Follow-ups: Why does it matter? • What would it cost?
#90
easy

What is one thing you would fix about the world if it were up to you?

Follow-ups: Where would you start? • What can we do today?
#91
easy

What is your favorite moment in our daily routine together?

Follow-ups: Why then? • What do we usually say?
#92
easy

What is one habit of mine you find endearing?

Follow-ups: When did you notice? • Do I know you watch?
#93
easy

What is your favorite thing I have ever cooked or brought you?

Follow-ups: Why that one? • When is round two?
#94
medium

What is one thing you do for us that you hope I notice?

Follow-ups: Why do you do it? • Should I notice more?
#95
easy

What is your favorite way to unwind together after work?

Follow-ups: Couch or outdoors? • What is on the playlist?
#96
easy

What is one thing you would add to our Sunday routine?

Follow-ups: Why that? • Which Sunday starts it?
#97
easy

What is your favorite snack to share with me?

Follow-ups: Why that one? • Who gets the last bite?
#98
easy

What is one thing you wish we did more on ordinary evenings?

Follow-ups: Why do we not? • What is in the way?
#99
easy

What is your favorite place to be next to me?

Follow-ups: Why there? • What do we usually do there?
#100
easy

What is one thing that makes missing me easier when we are apart?

Follow-ups: Why that? • How do you count down?
#101
easy

What is the sweetest dream you have had about us?

Follow-ups: What happened in it? • Should we make it real?
#102
easy

What is one text from me you saved and still reread?

Follow-ups: Why that one? • When do you reread it?
#103
easy

What is your favorite way for me to greet you?

Follow-ups: Why that way? • Who does it better?
#104
easy

What is one thing about us that still gives you butterflies?

Follow-ups: When did you last feel it? • Do I know I cause it?
#105
medium

What is one thing you want to tell me right now that you usually keep to yourself?

Follow-ups: Why now? • What is my answer?